JP6049630B2 - Ａｉｄｓを処置する為に有用な化合物 - Google Patents
Ａｉｄｓを処置する為に有用な化合物 Download PDFInfo
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- JP6049630B2 JP6049630B2 JP2013543948A JP2013543948A JP6049630B2 JP 6049630 B2 JP6049630 B2 JP 6049630B2 JP 2013543948 A JP2013543948 A JP 2013543948A JP 2013543948 A JP2013543948 A JP 2013543948A JP 6049630 B2 JP6049630 B2 JP 6049630B2
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- 150000001875 compounds Chemical class 0.000 title claims description 148
- 208000030507 AIDS Diseases 0.000 title claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 155
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 15
- -1 4-trifluoromethylpyridin-2-yl Chemical group 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 12
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 8
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 8
- 229940095064 tartrate Drugs 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- FPXYLXAMMKEESV-UHFFFAOYSA-N 2-n-[8-chloro-5-(2-morpholin-4-ylethoxy)quinolin-2-yl]-4-methylpyridine-2,3-diamine Chemical compound CC1=CC=NC(NC=2N=C3C(Cl)=CC=C(OCCN4CCOCC4)C3=CC=2)=C1N FPXYLXAMMKEESV-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- CDRBXJDVDCNVCR-UHFFFAOYSA-N 2-[4-[(8-chloroquinolin-2-yl)amino]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1NC1=CC=C(C=CC=C2Cl)C2=N1 CDRBXJDVDCNVCR-UHFFFAOYSA-N 0.000 claims description 5
- QJRSHFGNVORSNK-UHFFFAOYSA-N 8-chloro-5-(2-morpholin-4-ylethoxy)-n-[4-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine Chemical compound FC(F)(F)C1=CC=NC(NC=2N=C3C(Cl)=CC=C(OCCN4CCOCC4)C3=CC=2)=C1 QJRSHFGNVORSNK-UHFFFAOYSA-N 0.000 claims description 5
- VFTVHCSXVHUNNI-UHFFFAOYSA-N 8-chloro-5-(2-piperidin-1-ylethoxy)-n-[4-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine Chemical compound FC(F)(F)C1=CC=NC(NC=2N=C3C(Cl)=CC=C(OCCN4CCCCC4)C3=CC=2)=C1 VFTVHCSXVHUNNI-UHFFFAOYSA-N 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- GTEQYEMPPBFZQT-UHFFFAOYSA-N n-[3-methyl-2-[[4-(trifluoromethyl)pyridin-2-yl]amino]quinolin-5-yl]methanesulfonamide Chemical compound CC1=CC2=C(NS(C)(=O)=O)C=CC=C2N=C1NC1=CC(C(F)(F)F)=CC=N1 GTEQYEMPPBFZQT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- LWHIWNYBTZRFEP-UHFFFAOYSA-N 2-[(3-amino-4-methylpyridin-2-yl)amino]-5-(dimethylsulfamoylamino)-3-methylquinoline Chemical compound CC=1C=C2C(NS(=O)(=O)N(C)C)=CC=CC2=NC=1NC1=NC=CC(C)=C1N LWHIWNYBTZRFEP-UHFFFAOYSA-N 0.000 claims description 4
- DEOZHEHMTWAECR-UHFFFAOYSA-N 2-[(3-amino-4-methylpyridin-2-yl)amino]-8-chloro-5-(dimethylsulfamoylamino)-3-methylquinoline Chemical compound CC=1C=C2C(NS(=O)(=O)N(C)C)=CC=C(Cl)C2=NC=1NC1=NC=CC(C)=C1N DEOZHEHMTWAECR-UHFFFAOYSA-N 0.000 claims description 4
- STCNAZVMTAVEOZ-UHFFFAOYSA-N 2-[(3-amino-4-methylpyridin-2-yl)amino]-8-chloro-5-(dimethylsulfamoylamino)quinoline Chemical compound C=1C=C2C(NS(=O)(=O)N(C)C)=CC=C(Cl)C2=NC=1NC1=NC=CC(C)=C1N STCNAZVMTAVEOZ-UHFFFAOYSA-N 0.000 claims description 4
- FLGXDPRMCBJQQN-UHFFFAOYSA-N 2-[3-chloro-4-(trifluoromethoxy)anilino]-5-(dimethylsulfamoylamino)-3-methylquinoline Chemical compound CC=1C=C2C(NS(=O)(=O)N(C)C)=CC=CC2=NC=1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 FLGXDPRMCBJQQN-UHFFFAOYSA-N 0.000 claims description 4
- UCRMMFCBPWUBIE-UHFFFAOYSA-N 2-n-(3-amino-4-methylpyridin-2-yl)-8-chloro-3-methylquinoline-2,5-diamine Chemical compound CC1=CC=NC(NC=2C(=CC3=C(N)C=CC(Cl)=C3N=2)C)=C1N UCRMMFCBPWUBIE-UHFFFAOYSA-N 0.000 claims description 4
- YSOZQQVJTPFTMQ-UHFFFAOYSA-N 2-n-[8-chloro-3-methyl-5-(2-piperidin-1-ylethoxy)quinolin-2-yl]-4-methylpyridine-2,3-diamine Chemical compound CC1=CC=NC(NC=2C(=CC3=C(OCCN4CCCCC4)C=CC(Cl)=C3N=2)C)=C1N YSOZQQVJTPFTMQ-UHFFFAOYSA-N 0.000 claims description 4
- YGWZBJQQLKWYRQ-UHFFFAOYSA-N 8-chloro-2-[3-chloro-4-(trifluoromethoxy)anilino]-5-(dimethylsulfamoylamino)-3-methylquinoline Chemical compound CC=1C=C2C(NS(=O)(=O)N(C)C)=CC=C(Cl)C2=NC=1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 YGWZBJQQLKWYRQ-UHFFFAOYSA-N 0.000 claims description 4
- SHPNFUONBHWVSI-UHFFFAOYSA-N 8-chloro-2-[3-chloro-4-(trifluoromethoxy)anilino]-5-(dimethylsulfamoylamino)quinoline Chemical compound C=1C=C2C(NS(=O)(=O)N(C)C)=CC=C(Cl)C2=NC=1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 SHPNFUONBHWVSI-UHFFFAOYSA-N 0.000 claims description 4
- AUTPWUQQIPIRES-UHFFFAOYSA-N 8-chloro-2-n-[3-chloro-4-(trifluoromethoxy)phenyl]-3-methylquinoline-2,5-diamine Chemical compound CC1=CC2=C(N)C=CC(Cl)=C2N=C1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 AUTPWUQQIPIRES-UHFFFAOYSA-N 0.000 claims description 4
- LMKDXRLMPNWFJO-UHFFFAOYSA-N 8-chloro-3-methyl-2-n-[4-(trifluoromethyl)pyridin-2-yl]quinoline-2,5-diamine Chemical compound CC1=CC2=C(N)C=CC(Cl)=C2N=C1NC1=CC(C(F)(F)F)=CC=N1 LMKDXRLMPNWFJO-UHFFFAOYSA-N 0.000 claims description 4
- AFAFQKALERZORJ-UHFFFAOYSA-N 8-chloro-3-methyl-5-(2-piperidin-1-ylethoxy)-n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound C1=CC(Cl)=C2N=C(NC=3C=CC(OC(F)(F)F)=CC=3)C(C)=CC2=C1OCCN1CCCCC1 AFAFQKALERZORJ-UHFFFAOYSA-N 0.000 claims description 4
- SGTKQHGNCBULSG-UHFFFAOYSA-N 8-chloro-3-methyl-5-(2-piperidin-1-ylethoxy)-n-[4-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine Chemical compound C1=CC(Cl)=C2N=C(NC=3N=CC=C(C=3)C(F)(F)F)C(C)=CC2=C1OCCN1CCCCC1 SGTKQHGNCBULSG-UHFFFAOYSA-N 0.000 claims description 4
- GTIAINXNOUGZHA-UHFFFAOYSA-N 8-chloro-5-(2-piperidin-1-ylethoxy)-n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CC=C(C(OCCN2CCCCC2)=CC=C2Cl)C2=N1 GTIAINXNOUGZHA-UHFFFAOYSA-N 0.000 claims description 4
- ULCABPKCNGZGAZ-UHFFFAOYSA-N 8-chloro-n-(3-chloro-4-methoxyphenyl)-5-(2-morpholin-4-ylethoxy)quinolin-2-amine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=CC=C(C(OCCN2CCOCC2)=CC=C2Cl)C2=N1 ULCABPKCNGZGAZ-UHFFFAOYSA-N 0.000 claims description 4
- JREVCPFWYFNPGG-UHFFFAOYSA-N 8-chloro-n-[3-chloro-4-(trifluoromethoxy)phenyl]-5-(2-piperidin-1-ylethoxy)quinolin-2-amine Chemical compound C1=C(Cl)C(OC(F)(F)F)=CC=C1NC1=CC=C(C(OCCN2CCCCC2)=CC=C2Cl)C2=N1 JREVCPFWYFNPGG-UHFFFAOYSA-N 0.000 claims description 4
- IICKDKFFDMYJSX-UHFFFAOYSA-N 8-chloro-n-[4-methoxy-3-(2-morpholin-4-ylethoxy)phenyl]quinolin-2-amine Chemical compound COC1=CC=C(NC=2N=C3C(Cl)=CC=CC3=CC=2)C=C1OCCN1CCOCC1 IICKDKFFDMYJSX-UHFFFAOYSA-N 0.000 claims description 4
- IDQIZEYRBHTFBR-UHFFFAOYSA-N 8-chloro-n-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]quinolin-2-amine Chemical compound COC1=CC=C(NC=2N=C3C(Cl)=CC=CC3=CC=2)C=C1OCCN1CCCCC1 IDQIZEYRBHTFBR-UHFFFAOYSA-N 0.000 claims description 4
- SZNXWCCWQXCTNP-UHFFFAOYSA-N 8-chloro-n-[4-methoxy-3-[2-(2-methoxyethoxy)ethoxy]phenyl]quinolin-2-amine Chemical compound C1=C(OC)C(OCCOCCOC)=CC(NC=2N=C3C(Cl)=CC=CC3=CC=2)=C1 SZNXWCCWQXCTNP-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 4
- 229940072107 ascorbate Drugs 0.000 claims description 4
- 235000010323 ascorbic acid Nutrition 0.000 claims description 4
- 239000011668 ascorbic acid Substances 0.000 claims description 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- 230000001594 aberrant effect Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- HAVWZAULCLKNBA-UHFFFAOYSA-N n-[2-[3-chloro-4-(trifluoromethoxy)anilino]-3-methylquinolin-5-yl]methanesulfonamide Chemical compound CC1=CC2=C(NS(C)(=O)=O)C=CC=C2N=C1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 HAVWZAULCLKNBA-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 239000011541 reaction mixture Substances 0.000 description 45
- 230000002829 reductive effect Effects 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000012074 organic phase Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 11
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 108090000623 proteins and genes Proteins 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 8
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- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 7
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 7
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 7
- 108020004414 DNA Proteins 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- HRHZGVIXTTVSBL-UHFFFAOYSA-N 2-chloro-5-(2-piperidin-1-ylethoxy)aniline Chemical compound C1=C(Cl)C(N)=CC(OCCN2CCCCC2)=C1 HRHZGVIXTTVSBL-UHFFFAOYSA-N 0.000 description 4
- UWZBOFHBRKLFLJ-UHFFFAOYSA-N 4-[2-(4-chloro-3-nitrophenoxy)ethyl]piperidine Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(OCCC2CCNCC2)=C1 UWZBOFHBRKLFLJ-UHFFFAOYSA-N 0.000 description 4
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241000725303 Human immunodeficiency virus Species 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
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- 230000005856 abnormality Effects 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
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- BJFRVAWKEPFMEK-UHFFFAOYSA-N 2,8-dichloro-5-(2-piperidin-1-ylethoxy)quinoline Chemical compound C=1C=C(Cl)C2=NC(Cl)=CC=C2C=1OCCN1CCCCC1 BJFRVAWKEPFMEK-UHFFFAOYSA-N 0.000 description 3
- JUIKCULGDIZNDI-UHFFFAOYSA-N 4-chloro-3-nitrophenol Chemical compound OC1=CC=C(Cl)C([N+]([O-])=O)=C1 JUIKCULGDIZNDI-UHFFFAOYSA-N 0.000 description 3
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
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- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 2
- DKGXZFTVJFKCDM-FBMGVBCBSA-N (e)-n-[2-chloro-5-(2-piperidin-1-ylethoxy)phenyl]-2-methyl-3-phenylprop-2-enamide Chemical compound C=1C(OCCN2CCCCC2)=CC=C(Cl)C=1NC(=O)C(/C)=C/C1=CC=CC=C1 DKGXZFTVJFKCDM-FBMGVBCBSA-N 0.000 description 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 2
- CDDDASADVLSBGR-UHFFFAOYSA-N 2-chloro-5-(2-morpholin-4-ylethoxy)aniline Chemical compound C1=C(Cl)C(N)=CC(OCCN2CCOCC2)=C1 CDDDASADVLSBGR-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- AIDS & HIV (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10306417A EP2465502A1 (de) | 2010-12-15 | 2010-12-15 | Nützliche Verbindungen zur Behandlung von AIDS |
| EP10306417.6 | 2010-12-15 | ||
| PCT/IB2011/055643 WO2012080953A1 (en) | 2010-12-15 | 2011-12-13 | Compounds useful for treating aids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013545798A JP2013545798A (ja) | 2013-12-26 |
| JP2013545798A5 JP2013545798A5 (de) | 2015-02-05 |
| JP6049630B2 true JP6049630B2 (ja) | 2016-12-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013543948A Active JP6049630B2 (ja) | 2010-12-15 | 2011-12-13 | Ａｉｄｓを処置する為に有用な化合物 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US9061999B2 (de) |
| EP (2) | EP2465502A1 (de) |
| JP (1) | JP6049630B2 (de) |
| KR (1) | KR101749232B1 (de) |
| CN (1) | CN103415290B (de) |
| AR (1) | AR084277A1 (de) |
| AU (1) | AU2011342826B2 (de) |
| BR (1) | BR112013014943B1 (de) |
| CA (1) | CA2819317C (de) |
| CU (1) | CU20130080A7 (de) |
| DK (1) | DK2651416T3 (de) |
| ES (1) | ES2681539T3 (de) |
| HR (1) | HRP20181190T1 (de) |
| MX (1) | MX337258B (de) |
| PL (1) | PL2651416T3 (de) |
| PT (1) | PT2651416T (de) |
| RU (1) | RU2598845C2 (de) |
| WO (1) | WO2012080953A1 (de) |
| ZA (1) | ZA201303922B (de) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
| RU2567752C2 (ru) | 2009-06-12 | 2015-11-10 | Абивакс | Соединения, пригодные для лечения рака |
| EP2757161A1 (de) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 als ein Biomarker für virale Infektion |
| ES2898385T3 (es) * | 2013-07-05 | 2022-03-07 | Abivax | Compuestos bicíclicos útiles para el tratamiento de enfermedades causadas por retrovirus |
| EP2974729A1 (de) * | 2014-07-17 | 2016-01-20 | Abivax | Chinolinderivate zur Verwendung bei der Behandlung von Entzündungskrankheiten |
| EP2975034A1 (de) * | 2014-07-17 | 2016-01-20 | Abivax | Chinolinderivat zur Behandlung von Entzündungskrankheiten und AIDS |
| EP3058940A1 (de) | 2015-02-23 | 2016-08-24 | Abivax | Chinolin-Derivate zur Behandlung oder Vorbeugung von viralen Infektionen |
| EP3059236A1 (de) | 2015-02-23 | 2016-08-24 | Abivax | Neue Chinolinderivate zur Verwendung bei der Behandlung und Prävention von Virusinfektionen |
| EP3059591A1 (de) * | 2015-02-23 | 2016-08-24 | Abivax | Verfahren zum Screening von Verbindungen zur Behandlung oder Vorbeugung einer Virusinfektion oder einer mit Viren in Zusammenhang stehenden Erkrankung |
| WO2017034986A1 (en) * | 2015-08-21 | 2017-03-02 | University Of Kansas | Human tlr8-selective agonists |
| HRP20211779T1 (hr) | 2016-03-18 | 2022-03-04 | Prosynergia S.A.R.L. | Postupak priprave derivata kinolin-2-il-fenilamina i njihovih soli |
| KR101966351B1 (ko) * | 2016-06-08 | 2019-04-08 | 한국과학기술연구원 | 히스톤 메틸전달효소 저해용 퀴놀린 유도체 및 이의 용도 |
| EP3645029B1 (de) | 2017-06-26 | 2023-01-18 | Institut Pasteur | Behandlungen zur eliminierung von hiv-reservoirs und verringerung der viruslast |
| WO2019186277A1 (en) | 2018-03-28 | 2019-10-03 | Institut Pasteur | Ultrasensitive hiv-1 p24 detection assay |
| EP3594205A1 (de) | 2018-07-09 | 2020-01-15 | Abivax | Phenyl-n-aryl-derivate zur behandlung einer rna-virusinfektion |
| EP3594206A1 (de) * | 2018-07-09 | 2020-01-15 | Abivax | Phenyl-n-chinolin-derivate zur behandlung einer rna-virusinfektion |
| EP3669873A1 (de) | 2018-12-20 | 2020-06-24 | Abivax | Chinolinderivate zur verwendung bei der behandlung von entzündlichen krankheiten |
| EP3669874A1 (de) * | 2018-12-20 | 2020-06-24 | Abivax | Chinolinderivate zur verwendung bei der behandlung oder vorbeugung von krebs |
| WO2020128033A1 (en) | 2018-12-20 | 2020-06-25 | Institut Pasteur | Cellular metabolism of hiv-1 reservoir seeding in cd4+ t cells |
| CN109776498B (zh) * | 2019-03-13 | 2020-04-07 | 浙江永宁药业股份有限公司 | 一种西洛他唑的制备方法 |
| EP4063351A1 (de) * | 2021-03-26 | 2022-09-28 | Abivax | Verfahren zur herstellung von chinolinderivatverbindungen |
| EP4212156A1 (de) | 2022-01-13 | 2023-07-19 | Abivax | Kombination von 8-chlor-n-(4-trifluormethoxy)phenyl)chinolin-2-amin und dessen derivaten mit einem s1p-rezeptormodulator |
| EP4215196A1 (de) | 2022-01-24 | 2023-07-26 | Abivax | Kombination von 8-chlor-n-(4-trifluormethoxy)phenyl)chinolin-2-amin und dessen derivaten mit einem jak-inhibitor |
| WO2024109936A1 (zh) * | 2022-11-25 | 2024-05-30 | 江苏恒瑞医药股份有限公司 | 一种喹啉胺类化合物晶型及其制备方法 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US2419199A (en) * | 1945-02-09 | 1947-04-22 | Parke Davis & Co | Quinoline compounds and process of making same |
| FR2387229A1 (fr) | 1977-04-13 | 1978-11-10 | Anvar | Dipyrido (4,3-b) (3,4-f) indoles, procede d'obtention, application therapeutique et compositions pharmaceutiques les contenant |
| FR2436786A1 (fr) | 1978-09-21 | 1980-04-18 | Anvar | Nouveaux derives des pyrido (4,3-b) carbazoles (ellipticines), substitues en position 1 par une chaine polyaminee, leur obtention et leur application a titre de medicaments |
| JPS59501318A (ja) * | 1982-07-26 | 1984-07-26 | アメリカン ホスピタル サプライ コ−ポレ−シヨン | ヘテロアリ−ル置換アミノメチルベンゼン誘導体 |
| US4466965A (en) * | 1982-07-26 | 1984-08-21 | American Hospital Supply Corporation | Phthalazine compounds, compositions and use |
| FR2627493B1 (fr) | 1988-02-23 | 1991-10-31 | Sanofi Sa | Procede de preparation de derives d'isoquinoleine |
| FR2645861A1 (fr) | 1989-04-17 | 1990-10-19 | Inst Nat Sante Rech Med | Utilisation de dipyrido (4,3-b) (3,4-f) indoles pour la preparation de medicaments utiles pour le traitement du sida |
| ATE260099T1 (de) | 1999-04-05 | 2004-03-15 | Hope City | Neue hemmern von fortgeschrittenen glykosilierung-endprodukten |
| UA75055C2 (uk) * | 1999-11-30 | 2006-03-15 | Пфайзер Продактс Інк. | Похідні бензоімідазолу, що використовуються як антипроліферативний засіб, фармацевтична композиція на їх основі |
| ES2355472T3 (es) | 2002-05-22 | 2011-03-28 | Amgen Inc. | Derivados de aminopirimidina para su uso como ligandos del receptor vaniloide para el tratamiento del dolor. |
| AU2002950217A0 (en) | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
| MXPA05000827A (es) | 2002-07-19 | 2005-08-29 | Memory Pharm Corp | Inhibidores de fosfodiesterasa 4, incluyendo analogos de anilina y difenilamina n-sustituidos. |
| FR2849474B3 (fr) | 2002-12-27 | 2004-12-03 | Olivier Jean Noel Juin | Installation de transformation de l'energie cinetique d'un fluide en energie electrique |
| WO2004078731A1 (fr) * | 2003-03-06 | 2004-09-16 | 'chemical Diversity Research Institute', Ltd. | Acides quinoline-carboxyliques et leurs derives et bibliotheque focalisee |
| FR2859474B1 (fr) | 2003-09-04 | 2006-01-13 | Centre Nat Rech Scient | Utilisation de composes derives d'indole pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
| FR2859475A1 (fr) | 2003-09-04 | 2005-03-11 | Centre Nat Rech Scient | Utilisation de composes derives d'ellipticine et d'aza-ellipticine pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
| EP1853265B1 (de) | 2005-01-28 | 2016-01-27 | The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services | Farnesyltransferasehemmer zur behandlung von laminopathien, zellalterung und atherosklerose |
| FR2903312B1 (fr) | 2006-07-05 | 2008-09-26 | Univ Aix Marseille Ii | Utilisation d'inhibiteurs d'hmg-coa reductase et de farnesyl-pyrophosphate synthase dans la preparation d'un medicament |
| US8030487B2 (en) | 2006-07-07 | 2011-10-04 | Targegen, Inc. | 2-amino—5-substituted pyrimidine inhibitors |
| FR2912745A1 (fr) | 2007-02-19 | 2008-08-22 | Centre Nat Rech Scient | Nouveaux composes derives d'indole et compositions pharmaceutiques les contenant |
| WO2008115870A2 (en) | 2007-03-16 | 2008-09-25 | Mount Sinai School Of Medicine | Induction and/or maintenance of tumor dormancy by disruption of urokinase plasminogen activator receptor-integrin interaction |
| KR100961821B1 (ko) | 2007-05-17 | 2010-06-08 | 주식회사 엘지화학 | 신규한 안트라센 유도체 및 이를 이용한 유기전자소자 |
| KR20100053626A (ko) | 2007-08-15 | 2010-05-20 | 메모리 파마슈티칼스 코포레이션 | 5-ｈｔ6 수용체 친화성을 나타내는 3'-치환된 화합물 |
| FR2926297B1 (fr) | 2008-01-10 | 2013-03-08 | Centre Nat Rech Scient | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
| RU2567752C2 (ru) * | 2009-06-12 | 2015-11-10 | Абивакс | Соединения, пригодные для лечения рака |
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2010
- 2010-12-15 EP EP10306417A patent/EP2465502A1/de not_active Withdrawn
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2011
- 2011-12-13 US US13/993,990 patent/US9061999B2/en active Active
- 2011-12-13 DK DK11805230.7T patent/DK2651416T3/en active
- 2011-12-13 KR KR1020137018457A patent/KR101749232B1/ko active IP Right Grant
- 2011-12-13 RU RU2013126947/04A patent/RU2598845C2/ru active
- 2011-12-13 EP EP11805230.7A patent/EP2651416B1/de active Active
- 2011-12-13 BR BR112013014943-4A patent/BR112013014943B1/pt active IP Right Grant
- 2011-12-13 WO PCT/IB2011/055643 patent/WO2012080953A1/en active Application Filing
- 2011-12-13 CN CN201180060026.XA patent/CN103415290B/zh active Active
- 2011-12-13 JP JP2013543948A patent/JP6049630B2/ja active Active
- 2011-12-13 PL PL11805230T patent/PL2651416T3/pl unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2012080953A1 (en) | 2012-06-21 |
| PL2651416T3 (pl) | 2018-09-28 |
| DK2651416T3 (en) | 2018-08-06 |
| EP2651416A1 (de) | 2013-10-23 |
| CA2819317C (en) | 2017-02-28 |
| RU2598845C2 (ru) | 2016-09-27 |
| US20130267703A1 (en) | 2013-10-10 |
| AU2011342826B2 (en) | 2016-02-11 |
| PT2651416T (pt) | 2018-07-30 |
| KR101749232B1 (ko) | 2017-07-03 |
| CN103415290B (zh) | 2016-09-14 |
| JP2013545798A (ja) | 2013-12-26 |
| US9061999B2 (en) | 2015-06-23 |
| MX337258B (es) | 2016-02-22 |
| MX2013006322A (es) | 2013-10-25 |
| HRP20181190T1 (hr) | 2019-03-08 |
| ES2681539T3 (es) | 2018-09-13 |
| AU2011342826A1 (en) | 2013-07-04 |
| KR20140041402A (ko) | 2014-04-04 |
| BR112013014943A8 (pt) | 2018-06-12 |
| BR112013014943A2 (pt) | 2016-09-13 |
| BR112013014943B1 (pt) | 2022-05-03 |
| EP2651416B1 (de) | 2018-05-09 |
| EP2465502A1 (de) | 2012-06-20 |
| CU20130080A7 (es) | 2013-08-29 |
| CN103415290A (zh) | 2013-11-27 |
| ZA201303922B (en) | 2014-07-30 |
| RU2013126947A (ru) | 2015-01-20 |
| CA2819317A1 (en) | 2012-06-21 |
| AR084277A1 (es) | 2013-05-02 |
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